Ortho-oxymonoazo dye and process of making same.



CL] 13d f iil U sra'rns KART.- SGHIRldACHER, FRTEDRTCH SCHMIDT, CARL PRETZELL, AND WILLY SbHUMACHER, 01* HUGHST-UN-THE-MAIN; GERMANY, ASSIGNORS TU FARBWERKE, VOR-M. MEISTER, LUCIUS & BRTTNING, OF HQCHST-ON- THE-B'IAIN, GERMANY, A CORPORATION OF GERMANY.

Specification '0: Letters Patent.

Patented July e1, 1906.

Application and January 4., 1906. Serial No- 294.655.

To all whom/ it vim-y concern:

Be it known that we, KARL SCHIRMACHER, Ph. 1)., FRIEDRICH Somumr, Ph. 1)., and CARL PRETZELL, Ph. 1)., chemists, citizens of 5 the Empire ofGermany, and l VILLY SCHU- MAouER, Ph. D., chemist, a citizen of the United States of Americalresiding at Hochston-the-ldlain, Germany, have invented certain new and useful Improvements in'the Manu- I facture of Ortho-Oxymonoazo Dyestuffs, of

which the following is-a specification.

This invention relates to an improvement in. the manufacture of ortho-oxymonoazo dyestuffs from chromotropic acid and ori tho-amino-oxybenzene derivatives containing no sulfo group, which consists in allowing the diazo compounds. of saidaminophe- -nols to act on chromotropic acid not under the usual conditions, but in resence of hydroxids of elements being t e five middle members of the second group of the periodical systemnamely, magnesium, calciumstrontium, barium, and zinc.

The practical value of this process consists 2 5 in that a good yield of monoazo dyestuffs is obtained by combining c hromotropic acid with the diazotized ortho-amino-oxybenzene derivatives having no sulfo group in presence of said hydroxids, whereas no formation of dyestufi occurs at all or only insufficiently in presence of caustic alkalies. In presence of said hydroxids the transformation of said diazotized ortho-amino-oxybenzene derivatives with chromotropic acid occurs at ordi-r tained with ortho-aminophenols being at the same time derivatives of paranitranilini As orthdaminophenols are used in this process, for instance: ortho aminophenol, ortho amino para cresohortho am nometa Xylenol, para chloro ortho aminophenol, para bromo ortho aminophenol, 5 5 ortho para dichloro ortho aminophenol, ortho para dibromoaminophenol, chloroamino-oresols, I I

(OH:NI*I :CL:CH =1:2:6A and 1:2 1 1b, 6 acetamino-aniino phenols,

(OH:NI*I :NHAc-=1:2: i and 12:5,)

chloro-acetamino-aminophenols,

(OH:NH,:CL:NHA@:1:2:4:5 and 1121416, acetamino-aminocresol,

amino-oxybenzoic acid, 7

' (oirNn, noon 1 12 4, acetamino-amino-oxybenzoic acid,

cairn, :COOH:NHAc=1:2 14.15, amino-oxybenzoic acid methyl ester,

.(OHiNH zCOOcH 1:2 :4 and 12:5,) nitro-aminoph'enol,

on:NH,;No,.= 112e, nitro-aminocresol, oH;Nn,:oH,;No',= 1 1214s nitroohlor0-aminophen ol 8 5 4 (OH:NH :CL:NO =1:2:4:5,) nitro-amino-oxybenzoic acid,

' (01m n, :ooon :NO', 1 21415, 9

nitro-chloro-aminoo2iybenzoic acid,

on :Nn, :CL1NO :COOH so, 1 :2 14:5 :6.)

gravity and diazotized with 6.9 kilograms we of nitrite. The diazocomhiound is run into a solutionof thirty eight ilo rams of the disodium salt of 1.8-dioxyna thalene-2.6 disulfonic acid, which is stirre with'twentyfive kilograms of lime. After a few hours it is filtered and the dyestufl is isolated from the solution by adding hydrochloric acid and common salt. It is a owder of dark-bronze luster, soluble with a b ue-red color in water, in concentrated sulfuric acid with a red-blue color. On chrome mordanted wool it dyes a fast greenish-blue shade. In an acid-bath wool is dyed blue-red, and this shadeturns to blue when treated with chromates.

'Having now described our invention, what we claim is 1. The process herein described for the manufacture of ortho-oxymonoazo dyestufis from chromotropic acid and diazotized orthov ino -oxybenzene derivatives, being at the 3 amino-oxybenzene derivatives containing no sulfo group, which consists in allowing said components to act on .each other in resence of hydroxids of elements being-the Eve middle members of the second group of the periodic'system.

2. The process herein described for the manufacture of ortho-oXyazo dyestufls from chromotropic acid and diazotized ortho-amsame time derivatives of the para-nitranilin which consists in allowing sald components to act on each other in presence of hydroXids of elements being the middle members of the second group of the periodic system.

I 3. The process herein described for the manufacture of ortho-o'xyazo dyestuffs from vchromotropic acid and diazotized ortho-amino-meta-nitrophenol,

which consists in allowing the said components to act on each other in presence of ydrate of lime. 4. As new product, the azo dyestufl which corresponds to the formula KARL SCHIRMACHER. FRIEDRICH SCHMIDT.

CARL PRETZELL. WILLY SCHUMACHER.

Witnesses JEAN GRUNI), CARL GRUND. 

